mi have been doing the 3 months here and 3 months in Florida thingy for 4 years now......and it works nice for mi
mi find after after a couple months/3 months that mi getting mi fill of paradise and need a break.....
though next Winter or sooner mi gotta make a decision if mi will continue the 3 month thingy or stay longer since mi fully retire....

beach is the high rent district and don't know of any places for $500 month........
with dat said der a lot of places on da West End for extended stays....
typically the extended rates go from $30,000J's and up......but $30,000J plus utilities is pretty common...so $500 well within your range
best to do your research and go door knocking when you reach next time.......
mi would never lock into sumthin here without seeing it.......

Cool Runnings, Marko